2,2-Dimethylmorpholine → 2,2-Dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine

HRID 1431384ノート

反応式

HRID 1431384 の反応式
Cl[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:17][C:18]1([CH3:24])[O:23][CH2:22][CH2:21][NH:20][CH2:19]1.C1(P(C2CCCCC2)C2(C(C)C)CC(C(C)C)=CC(C(C)C)=C2C2C=CC=CC=2)CCCCC1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[CH3:17][C:18]1([CH3:24])[O:23][CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[N:6][C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=2)[CH2:19]1

参加物

7

反応物 4

HCID 189596742,2-DimethylmorpholineHCID 23676156Sodium t-butoxideHCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholineHCID 672859322-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl

生成物 1

HCID 596311902,2-Dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒

実験手順

A solution of 4-(5-chloro-3-nitropyridin-2-yl)morpholine (850 mg, 3.49 mmol; described herein), 2,2-dimethylmorpholine (480 μL, 4180 μmol), tris(dibenzylideneacetone)dipalladium(o) (224 mg, 0.244 mmol), 2-(dicyclohexylphosphino)-2,4,6,-tri-i-propyl-1,1-biphenyl (249 mg, 0.523 mmol), sodium 2-methylpropan-2-olate (671 mg, 6.98 mmol), and toluene (517 mL) was refluxed overnight, then cooled to rt and concentrated. The resulting residue was taken up in EtOAc, washed with satd aq. sodium bicarbonate and brine, then the organic layer dried (magnesium sulfate) and concentrated. Column chromatography afforded 2,2-dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine as a red solid. Mass Spectrum (ESI) m/e=323.2 (M+1).

後処理

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated
  3. washwashed with satd aq. sodium bicarbonate and brine
  4. dry with materialthe organic layer dried (magnesium sulfate)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-c28460f047664701b304d247e5cef496
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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